This invention relates to new chemical compounds. More particularly it relates to new chemical compounds which are of value as antibacterial agents. These new antibacterial agents are bis-esters of methanediol and 1,1-ethanediol, in which one hydroxy group of the diol has been esterified with the carboxy group of a 6-acylaminopenicillanic acid, and the other hydroxy group of the given diol has been esterified with the carboxy group of 2-beta-acetoxymethyl-2-alpha-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxide.
In addition, this invention relates to the 6-aminopenicillanoyloxymethyl and the 1-(6-aminopenicillanoyloxy)ethyl esters of 2-acetoxymethyl-2-beta-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxide. These latter compounds are useful as intermediates to the antibacterial agents of this invention.
Still further, this invention relates to certain halomethyl, alkylsulfonyloxymethyl, arylsulfonyloxymethyl, 1-haloethyl, 1-(alkylsulfonyloxy)ethyl and 1-(arylsulfonyloxy)ethyl esters of 2-beta-acetoxymethyl-2-alpha-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxide. Said latter compounds are also useful as intermediates to the antibacterial agents of this invention.
U.S. Pat. No. 4,244,951 and Belgium Pat. No. 881,675 disclose bis-esters of 1,1-alkanediols in which one of the hydroxy groups of the 1,1-alkanediol has been esterified with the carboxy group of a beta-lactamase inhibitor, e.g. penicillanic acid 1,1-dioxide. Said United States and Belgian patents also disclose a variety of intermediates to said bis-esters of 1,1-alkanediols.
The antibacterial agents of the present invention are efficiently absorbed from the gastrointestinal tract of mammals, and after absorption they are transformed into a 6-acylaminopenicillanic acid and 2-beta-acetoxymethyl-2-alpha-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxide.